I am reorganizing music like a crazy person, now that I have a 500GB external drive for it to sit on. When I first started actually collecting digital music - which I hadn’t really done before - it was in a kind of haphazard manner, with a bunch of tunes all thrown into a directory. When I started ripping my own CDs, I made categories by artist for them, but I was still kind of lax with it. But now I’m putting everything into a category by artist, except for “Various Artists” CDs which are organized by album. The point is to avoid downloading duplicates, although I haven’t found a whole lot of duplicates yet as I’ve been organizing.

I’m pretty sure iTunes is going to go insane when I fire it up and try to sync - it’s going to say it can’t find anything! I don’t have a lot of songs rated or with “number of times played” so maybe I should just start a whole new library, I dunno. I need to delete a bunch of podcasts, too…I don’t need those hanging around.